19 High Street, Middlefield, CT 06455
Property image
Property image
NEW
COMING SOON 8/14
1.2 ACRES

19 High Street
Middlefield, CT 06455

  • 2 Beds
  • 1.5 Baths
  • 4,073 sqft (on 1.20 acres)

$850,000

Est. Mortgage $5,777/mo*
Get Pre-Qualified

$850,000

Est. Mortgage $5,777/mo*
Get Pre-Qualified
2 Beds
1.5 Baths
4,073 sqft
(on 1.20 acres)

Home Highlights

Parking
Garage
Outdoor
Patio
Climate Control
Heating only
Price/Sqft
$209
Listed
Less than a day ago

Local Information

  • Map ViewExplore the area around 19 High Street.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Older than America, the historic Chilson Bailey House offers a rare opportunity to own a true circa 1750 center chimney Colonial while enjoying the comfort of a beautifully designed 2008 addition. The original 1750 home is not currently livable and is ready for renovation, providing the next owner the chance to restore an authentic piece of Connecticut history at their own pace. Everyday living takes place in the thoughtfully designed 2009 addition featuring 2,963 square feet of living space, a spacious country kitchen with an oversized island, soaring great room with a floor-to-ceiling stone fireplace, wide-plank pine floors, a first-floor primary suite, and an expansive second-floor loft ideal for a home office, family room, or creative space. Outside, the impressive barn and detached garage provide exceptional space for car collectors, hobbyists, contractors, woodworking enthusiasts, or anyone needing room for projects, equipment, or recreational vehicles. Major improvements-including the addition, detached garage, septic system, 200-amp electrical service, lease solar, and new windows in the original home-have already been completed, allowing you to focus on restoring the historic heart of this remarkable property. Whether you're passionate about historic preservation or simply searching for a property unlike any other, this is your opportunity to restore a landmark while enjoying the comforts of modern living from day one.

Home Details for 19 High Street

Interior Features

Interior Details
Basement: FullNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4073 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Refrigerator, DishwasherDishwasherLaundry: Main LevelRefrigerator
Heating & Cooling
Heating: Hydro Air,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Hydro Air
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Door: French Doors

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: PatioOther Structures: Barn(s)Foundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 12Number of Covered Spaces: 12No CarportHas a GarageNo Attached GarageParking Spaces: 12Parking: Barn,Detached
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 4073 Square Feet

Days on Market

Days on Market: <1 day on Trulia

Property Information

Year Built
Year Built: 1750
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Antique
Building
Construction Materials: Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1000699

Price & Status

Price
List Price: $850,000Price Per Sqft: $209
Status Change & Dates
Possession Timing: Negotiable

Active Status

MLS Status: Coming Soon

Location

Direction & Address
City: Middlefield
School Information
Elementary School: John LymanHigh School: Coginchaug Regional

Agent Information

Listing Agent
Listing ID: 24196454

Building

Building Area
Building Area: 4073 Square Feet

Community

Community Features: Golf, Lake, Park, Putting Green

HOA

No HOA

Lot Information

Lot Area: 1.2 Acres

Miscellaneous

BasementMls Number: 24196454Attic: Walk-upAttribution Contact: (860) 918-4580Above Grade Unfinished Area: 4073Activation Date: Fri Aug 14 2026

Additional Information

GolfLakeParkPutting Green
Last check for updates: about 3 hours ago
Listing courtesy of Debbie D. Huscher, (860) 918-4580
Real Broker CT, LLC, (860) 918-4580
Source: Smart MLS, MLS#24196454
Also Listed on Smart MLS.

Market trends in Middlefield

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
5

Price History for 19 High Street

DatePriceEventSource
12/28/2004$138,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax$9,900
Assessment$332,200
Home facts updated by county records

Comparable Sales for 19 High Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
17 Esther Drive, Middlefield, CT
0.34
Single-Family Home
$465,528
04/30/26
3
2.5
2,152
45 Dwight Road, Middlefield, CT
0.23
Single-Family Home
$475,000
04/27/26
3
1.5
1,554
30 Dwight Road, Middlefield, CT
0.31
Single-Family Home
$409,500
09/03/25
3
1.5
1,960
32 Powder Hill Road, Middlefield, CT
0.40
Single-Family Home
$550,000
08/28/25
3
2.5
2,812
6 Lakeview Place, Middlefield, CT
0.22
Single-Family Home
$291,500
05/01/26
2
1
756
121 Powder Hill Road, Middlefield, CT
0.77
Single-Family Home
$246,000
05/27/26
3
1.5
1,642
239 Baileyville Road, Middlefield, CT
0.22
Single-Family Home
$310,000
09/18/25
2
1.5
610
51 Louis Road, Middlefield, CT
0.55
Single-Family Home
$785,000
06/19/26
5
4
3,911
20 Mack Road, Middlefield, CT
0.63
Single-Family Home
$415,000
09/30/25
4
3.5
2,776
51 Lake Shore Drive, Middlefield, CT
0.48
Single-Family Home
$324,000
09/19/25
2
1
1,258

Nearby homes

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Assigned Schools

These are the assigned schools for 19 High Street.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Middlefield

At least 15 Trulia users voted on each feature.

  • 100 % Say there's holiday spirit

  • 100 % Say car is needed

  • 93 % Say yards are well-kept

  • 90 % Say it's dog friendly

  • 84 % Say parking is easy

  • 83 % Say people would walk alone at night

  • 81 % Say there's wildlife

  • 76 % Say kids play outside

  • 75 % Say it's quiet

  • 63 % Say neighbors are friendly

  • 58 % Say they plan to stay for at least 5 years

  • 50 % Say there are community events

  • 39 % Say it's walkable to restaurants

  • 19 % Say streets are well-lit

  • 12 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Christina
    "Great area to walk dogs and meet other dogs. We have a dog park as well and lots of walking and hiking trails "
    0
    Flag
  • Kelican8621
    "Lived here for 7-8 years. Elementary through high school years actually. Great place to grow up and raise a family. The park in the center of town is well maintained and continually is adding additional activities for the community "
    1
    Flag
  • Mazie123b
    "Middlefield is a great town. Everyone is very friendly and neighborly and it is overall a safe place to live. "
    1
    Flag
  • Beannbeann
    "Great neighborhood. Every one is friendly. Nice area to take walks. No car traffic. And only a few miles from shopping. "
    1
    Flag
  • Beannbeann
    "Great area to walk your dog around and there’s a dog park within two miles from this area by the lake"
    0
    Flag
  • Beannbeann
    "Great small town to raise children. Close to shopping and highways but far enough away that you feel your living in the country. "
    0
    Flag
  • Beannbeann
    "I’ve lived in this neighborhood for 18 years now and it’s great. Friendly neighbors. Houses are close enough to walk from house to house but most properties are at least a half acre or more. Great area for kids to grow up in. "
    0
    Flag
  • Mazie B.
    "People are constantly walking their dogs around the neighborhood. There are no sidewalks, but there are plenty of nice, quiet, open streets. "
    0
    Flag
  • Debi W.
    "Lived here almost all my life - love small-town living! You can always count on your neighbors to be there for you. Quiet and tranquil - but close to big cities!"
    3
    Flag
  • Lisareed2018
    "My family has lived in this town for more than 100 years. I love this little town. Good schools, great homeownership ratio, nice homes with good sized yards, skiing, recreation, nestled in the country, but close enough to cities, too! "
    0
    Flag

LGBTQ Local Legal Protections

Debbie D. Huscher, Real Broker CT, LLC, (860) 918-4580
Agent Phone: (860) 918-4580
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
19 High Street, Middlefield, CT 06455 is a 2 bedroom, 2 bathroom, 4,073 sqft single-family home built in 1750. This property is currently available for sale and was listed by Smart MLS on Aug 3, 2026. The MLS # for this home is MLS# 24196454.